Transformative Leadership Conversations with Winnie da Silva

Winnie da Silva
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Transformative Leadership Conversations with Winnie da Silva

Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

  1. Dream Big, Iterate Fast with Medha Agarwal

    MAR 26

    Dream Big, Iterate Fast with Medha Agarwal

    “No one works as hard as founders do. They’re operating on another level of intensity.” - Medha Agarwal

    28 min
  2. Aligning Founder Vision to Business Strategy with Stephanie Unwin

    MAR 19

    Aligning Founder Vision to Business Strategy with Stephanie Unwin

    "My role is catching the ideas and making them happen." – Stephanie UnwinIs your leadership moving forward, or are you just keeping busy?In the fast-paced world of executive leadership and entrepreneurship, it can feel impossible to carve out time to think strategically. But what if making space for reflection isn’t a luxury—it’s the key to unlocking long-term success? In this episode of Transformative Leadership Conversations, I sit down with Stephanie Unwin, a seasoned executive and business leader, to explore how prioritizing strategic thinking not only makes you a stronger leader, but also helps you steer your company toward sustainable growth.Stephanie opens up about the importance of deliberately carving out time for reflection, recharge, and deep thinking—ensuring that leadership isn't just about constant action but also about intentional decision-making that shapes the future of the business.You'll hear us discuss:* Why carving out time to think is not a “nice to have”—it’s a leadership necessity. As an executive, it’s easy to get swept up in the whirlwind of daily demands—meetings, emails, and urgent decisions that take up most of your day. However, without setting aside dedicated time to reflect, refine strategy, and gather your thoughts, leaders risk losing sight of the bigger picture.* The secret to balancing high-energy execution with moments of clarity. Leading a company often feels like an unending sprint. While constant action and execution are important, Stephanie explains how never taking a step back to pause and think can lead to burnout, decision fatigue, and reactive leadership.* Why founders and executives must stay aligned on vision, values, and risk-taking. Whether you’re working for a founder or running a startup yourself, one of the most critical components of leadership is alignment. Stephanie dives deep into why executives must ensure that their vision, values, and approach to risk-taking are in sync with the founders or leadership team.* How to navigate change without losing sight of the bigger picture. The business world is in a constant state of flux—markets shift, technologies evolve, and customer demands change. Leaders who resist change or get bogged down by every shift risk falling behind. Stephanie shares her approach to staying agile, adapting to changes, and continuously innovating without compromising the company's core mission and values. .* The underestimated power of trusting your team and leveraging their insights. No leader has all the answers, and the most effective leaders are those who recognize the importance of collective intelligence. Stephanie highlights how fostering a culture where team members feel empowered to share ideas, challenge assumptions, and contribute to strategic discussions can greatly enhance decision-making.

    40 min
  3. Working Successfully with Founders with Winnie da Silva

    MAR 12

    Working Successfully with Founders with Winnie da Silva

    What makes some founders incredible leaders—and others impossible to work with? They are visionaries, but are they always great leaders? Founders bring passion, vision, and drive, but they can also be intense, stubborn, and relentless. Working with them isn’t just about executing their vision—it’s about knowing when to support, when to challenge, and how to scale alongside them. So how do you do that effectively?In this episode of Transformative Leadership Conversations, I dive into what makes founders tick, the challenges they face, and how you can be a strategic partner in their success. Whether you work for, with, or invest in a founder, understanding their mindset is key to building a strong and successful relationship.You’ll hear me discuss:* The surprising data behind founders—Forget the stereotype of the young tech genius. The average founder is older than you might think, and startups with multiple founders tend to outperform solo-led businesses. I break down what the numbers actually tell us about who succeeds and why.* The four founder archetypes—Inventors generate endless ideas but struggle with execution. Drivers push forward with sheer determination but risk burnout. Builders create structure and scalability but may resist change. Guides lead with vision and culture but can be too hands-off. I’ll explain how to work with each type effectively.* How to challenge a founder without clashing—The best partners don’t just follow orders; they push founders to grow. I share strategies for helping founders see blind spots, make better decisions, and scale successfully—without stepping on toes.* The pitfalls founders face (and how to help them avoid them)—From burnout to hiring mistakes to emotional attachment that clouds judgment, many founders struggle to transition from startup hustle to sustainable leadership. I’ll highlight key risks and how you can help navigate them.* What makes working with founders so exciting (and tough)—Founders move fast, take risks, and embrace uncertainty. That energy is contagious, but it can also be exhausting. I’ll share what I love about working with founders—and the biggest challenges to watch for.ResourcesWinnie da Silva on (https://www.linkedin.com/in/winnie-da-silva-1b8414/)LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | (https://www.winniedasilva.com/)On the Web (https://www.winniedasilva.com/) |

    16 min
  4. Neglected Leadership Characteristic #3: Courage in the Face of Fear with Winnie da Silva

    FEB 26

    Neglected Leadership Characteristic #3: Courage in the Face of Fear with Winnie da Silva

    “Leadership without courage isn't leadership at all, but courage without integrity is dangerous.’’ - Winnie da SilvaWhat if your fear was the key to unlocking your greatest leadership potential? In this episode of Transformative Leadership Conversations, I explore the often-overlooked power of fear in leadership. Fear is something all leaders face, but it's not the fear itself that defines us—it's how we respond to it. You’ll hear me discuss how we can transform fear from a roadblock into a powerful catalyst for courageous leadership. The question isn’t whether you’re afraid, it’s what you choose to do in the face of that fear.As we navigate these turbulent times, it’s more important than ever to lead with courage, not just for yourself but for your team. Fear will always be a part of leadership, but what if you could choose courage instead of being paralyzed by fear?You’ll hear me discuss:* The Neuroscience of Fear: I break down how your brain responds to fear and why your body treats psychological threats just like physical ones. I’ll explain how your brain’s stress response can hijack your decision-making and what this means for leaders in high-pressure situations.* The Role of Courage in Leadership: Courage isn’t about eliminating fear—it’s about navigating it. I'll explain why leadership without courage isn't really leadership at all, and why courage without integrity is dangerous. Courage is a skill, not a trait, and it’s essential for effective leadership, especially in times of uncertainty and fear.* The Brain’s Built-in Mechanism for Courage: Neuroscience reveals that our brains are wired to react to fear, but the good news is we can override that natural response. I'll show you how activating your prefrontal cortex allows you to make better decisions, even when fear is present. Courage isn’t the absence of fear—it’s the ability to act in spite of it.* Whistleblowing as an Act of Courage: Using the example of Stephen May, a whistleblower from Purdue Pharma, I’ll discuss how standing up against unethical practices takes immense courage, even when the cost is high. You’ll hear how speaking truth to power can lead to transformational change, even when the path isn’t easy or well-received.* Practical Strategies to Cultivate Courage: Finally, I’ll offer practical steps to help you develop and strengthen your own courage. From identifying where fear is holding you back to taking small, intentional steps, I’ll guide you on how to confront fear head-on and train yourself to be a braver, more effective leader.ResourcesWinnie da Silva on

    20 min
  5. Neglected Leadership Characteristic #2: Reframing Humility

    FEB 19

    Neglected Leadership Characteristic #2: Reframing Humility

    "The old model of leadership, commanding, dominating, and never admitting failure, is outdated, and more importantly, it's ultimately ineffective." - Winnie da SilvaIs humility the secret weapon some leaders are overlooking? In today’s fast-paced world, we’re taught to believe that the most successful leaders are the loudest, the boldest, and the most aggressive. But what if humility, often seen as a weakness, is actually the missing ingredient to becoming a more effective and respected leader? In this episode of Transformative Leadership Conversations, the second one in the Neglected Leadership Characteristics series, I’m challenging the traditional view of leadership and showing how humility can drive better business results, strengthen relationships, and foster a culture of trust and innovation.You’ll hear me discuss:* Why humility isn’t weakness: I unpack how humble leaders aren’t passive or pushovers, but confident, decisive individuals who are willing to take a stand even when it’s unpopular. Humility doesn’t mean avoiding conflict—it means making thoughtful, informed decisions with integrity.* The power of reframing humility: Today, humility is often seen as outdated or even embarrassing, especially in industries that reward aggressive self-promotion. I’ll explore how rebranding humility as a strength can help leaders build stronger teams and make better decisions in uncertain times.* The critical difference between humility and arrogance: Arrogance can alienate teams and cloud judgment, while humility creates trust and respect. I’ll share how embracing humility can lead to higher engagement, stronger relationships, and more creative solutions in the workplace.* How humility fuels innovation: I’ll dive into how humble leaders actively seek out diverse perspectives, encourage experimentation, and admit they don’t have all the answers. In a world that’s constantly changing, this mindset is key to staying ahead of the competition and creating lasting impact.* Practical tips for embracing humility in your leadership style: It’s not enough to just talk about humility—I’ll share actionable strategies you can use to incorporate humility into your daily leadership practice, such as seeking feedback, admitting mistakes, elevating others’ contributions, and staying grounded despite success.* Why humility might be the antidote to today’s leadership challenges: From disorientation to fear and uncertainty, we’re living in a time when traditional approaches to leadership are failing. I’ll explain how humility could be the solution to navigating these complex challenges while building a stronger, more resilient organization.Resources

    23 min
  6. Neglected Leadership Characteristic #1: Collaboration Through Disagreement

    FEB 12

    Neglected Leadership Characteristic #1: Collaboration Through Disagreement

    "Encouraging disagreement strengthens decision-making, challenges blind spots, and creates an environment where people feel heard." - Winnie da SilvaWhat if avoiding disagreement is actually holding you back? Most of us instinctively avoid conflict. We’re taught that disagreeing can damage relationships, create tension, or make us look difficult. But what if I told you that the way we approach disagreement could be the key to making better decisions, building stronger teams, and gaining real influence? The truth is, the most successful people don’t run from disagreement—they master it. In this episode of Transformative Leadership Conversations, I explore how to turn conflict into a tool for growth rather than a source of frustration. I break down why disagreement is not the enemy, why avoiding it can be more damaging than facing it, and how the best leaders use it to their advantage.You’ll hear me discuss:* Why avoiding disagreement is riskier than facing it – The hidden dangers of keeping quiet and why people often regret not speaking up more than they regret engaging in a debate.* How Abraham Lincoln turned political rivals into trusted allies – A look at his Team of Rivals approach and how bringing opposing voices together led to better decisions.* The difference between arguing to win vs. arguing to learn – Why treating disagreement as a battle is the fastest way to lose credibility, and what to do instead.* Why true influence isn’t about power—it’s about how you disagree – The people who hold the most influence aren’t necessarily the ones in charge, but the ones who challenge ideas the right way.* The 3 common ways people handle disagreement—and the one that actually works – Do you avoid, attack, or adapt? Understanding these patterns will help you shift toward more productive conversations.* How to make disagreements feel less personal and more productive – A simple mindset shift that reduces defensiveness and keeps the conversation focused on solutions.* Practical techniques for disagreeing without damaging relationships – Real strategies to express your point of view while still keeping mutual respect intact.

    24 min
  7. Motivation, Identity, and Impact with Nikhil Paul

    JAN 29

    Motivation, Identity, and Impact with Nikhil Paul

    "Motivation starts with identity—when you believe in the story you’re telling yourself, the actions follow." - Nikhil Paul

    51 min
  8. Fueling Growth with Aligned Motivation with James Thorman

    JAN 22

    Fueling Growth with Aligned Motivation with James Thorman

    "When you align individual motivation with the broader mission, that’s when magic happens and teams thrive.” - James Thorman...

    55 min
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Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

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